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Volumn 44, Issue 11, 1988, Pages 3119-3126

1,3-Dipolar cycloaddition reactions of pyrazolidinium ylides with vinyl sulfones. A regioselective synthesis of bicyclic pyrazolidinone antibacterial agents

(6) Jungheim, Louis N a Barnett, Charles J a Gray, Joseph E a Horcher, Linus H a Shepherd, Timothy A a Sigmund, Sandra K a

a ELI LILLY AND COMPANY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001507540 PISSN: 00404020 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4020(01)85943-3 Document Type: Article

Times cited : (33)

References (23)

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- We thank these authors for sharing their results prior to publication and for providing us with samples of vinyl sulfoxides corresponding to 5a-(E) and 5c-(Z). Preliminary efforts to cycloadd these sulfoxides gave inferior results.
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9
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- Darstellung, Konfigurationen und NMR-Daten der S�uren CH3(SR) ? CHCOOH (R ? C6H5, CH2C6H5, CH2COOH)
- For examples confirmed by NOE experiments see:
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- 3): δ7.76 (d,2,J=9); 7.34 (d,2,J=9); 7.32 (d,l,J=16); 6.78 (d,l,J=16); 6.12-5.68 (m,1); 5.42-5.17 (m,2); 4.66 (d,l,J=6); 2.43 (s,3)
- (1977) Zh. Org. Khim. , vol.13 , pp. 1418
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12
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- For other cases of stereospecific elimination of β-subtituted sulfones see, W. Bartmann, E. Winterfeldt, Elsevier North-Holland, New York
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13
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- Bromination of 11b with bromine in the absence of triethylamine produced an unfavorable mixture of 5b-(E) and a product of dibromination of the methyl group of the acetyl moiety.

14
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- D. Neel Lilly Research laboratories unpublished observations.

15
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- 2 has observed that cis-1-(phenylsulfonyl)-2-(trimethylsilyl) ethylene was less reactive towards cycloaddition with dienes than the trans isomer.

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- Jungheim, L.N.; Holmes, R.E. “4-Substituted Diazolidinones.” Eur. Pat. Appl. 202,795, 11/26/86

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- The C-3 cyano nucleus was first prepared by a regiochemically unambiguous route. Acylated analogs of 3e have been prepared and were found to exhibit greater antibacterial potency than LY186826. R.J Ternansky Lilly Research Laboratories, unpublished results.

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22
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- 2 elution) of the corresponding sulfoxides (method of J.E. Munroe and W.J. Hornback reference 4), followed by peracid oxidation to the sulfones.

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